5-Chloro-quinolin-8-yl furan-2-carboxyl-ate.

In the title compound, C14H8ClNO3, the central ester CO2 group is twisted away from the quinoline and furoyl rings by 57.46 (5) and 2.0 (1)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming chains in [001].

Related literature

For medicinal, anti­fungal, anti­bacterial, anti­cancer and luminiscent properties of the quinoline ring, see: Somvanshi et al. (2008 ▶), Biavatti et al. (2002 ▶), Towers et al. (1981 ▶), Shen et al. (1999 ▶) and Montes et al. (2006 ▶), respectively. For similar structures, see: Lei (2006 ▶; 2007 ▶). For hydrogen-bonding notation, see: Etter (1990 ▶); Nardelli (1995 ▶).

Experimental

Crystal data

C14H8ClNO3

M = 273.66

Monoclinic,

a = 4.0714 (1) Å

b = 23.7463 (7) Å

c = 12.7698 (4) Å

β = 102.113 (1)°

V = 1207.11 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.35 × 0.09 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer

4385 measured reflections

2440 independent reflections

1906 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.03

2440 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005667/gg2111sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005667/gg2111Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005667/gg2111Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H8ClNO3	F(000) = 560
Mr = 273.66	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Melting point: 389(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.0714 (1) Å	Cell parameters from 2589 reflections
b = 23.7463 (7) Å	θ = 3.1–26.3°
c = 12.7698 (4) Å	µ = 0.32 mm−1
β = 102.113 (1)°	T = 295 K
V = 1207.11 (6) Å3	Needle, colourless
Z = 4	0.35 × 0.09 × 0.09 mm

Nonius KappaCCD diffractometer	1906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 26.3°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −5→5
4385 measured reflections	k = −29→27
2440 independent reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.2631P] where P = (Fo2 + 2Fc2)/3
2440 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.86765 (17)	0.10906 (3)	1.01429 (4)	0.0852 (3)
O3	−0.0985 (4)	0.21415 (5)	0.32844 (10)	0.0617 (4)
O2	0.3216 (4)	0.22368 (6)	0.53277 (11)	0.0735 (4)
O1	0.1366 (3)	0.13797 (5)	0.56894 (10)	0.0590 (4)
N1	0.5632 (4)	0.05097 (6)	0.61584 (11)	0.0518 (4)
C9	0.5359 (4)	0.08729 (7)	0.69653 (13)	0.0442 (4)
C3	0.9075 (5)	0.02976 (8)	0.82623 (15)	0.0578 (5)
H3	1.0231	0.0221	0.8956	0.069*
C4	0.7073 (4)	0.07857 (7)	0.80464 (13)	0.0470 (4)
C10	0.1468 (4)	0.18356 (7)	0.50701 (13)	0.0471 (4)
C8	0.3285 (5)	0.13513 (7)	0.67304 (14)	0.0491 (4)
C6	0.4679 (5)	0.16529 (8)	0.85564 (15)	0.0592 (5)
H6	0.4485	0.1917	0.9078	0.071*
C2	0.9304 (5)	−0.00590 (9)	0.74516 (17)	0.0630 (5)
H2	1.0611	−0.0383	0.7585	0.076*
C12	−0.2882 (5)	0.13064 (8)	0.36831 (15)	0.0540 (4)
H12	−0.3217	0.0982	0.4054	0.065*
C11	−0.0828 (4)	0.17374 (7)	0.40520 (13)	0.0456 (4)
C7	0.2944 (5)	0.17315 (8)	0.74910 (16)	0.0568 (5)
H7	0.1566	0.2044	0.7310	0.068*
C14	−0.3227 (6)	0.19455 (10)	0.24173 (16)	0.0668 (6)
H14	−0.3837	0.2136	0.1769	0.080*
C5	0.6638 (5)	0.11902 (8)	0.88183 (14)	0.0540 (5)
C1	0.7556 (5)	0.00645 (8)	0.64139 (16)	0.0592 (5)
H1	0.7767	−0.0184	0.5869	0.071*
C13	−0.4431 (5)	0.14454 (10)	0.26179 (16)	0.0654 (5)
H13	−0.5989	0.1229	0.2149	0.078*

	U11	U22	U33	U12	U13	U23
Cl1	0.1006 (5)	0.1148 (5)	0.0337 (3)	0.0015 (4)	−0.0007 (3)	−0.0047 (3)
O3	0.0868 (9)	0.0501 (7)	0.0449 (7)	0.0020 (6)	0.0064 (7)	0.0084 (5)
O2	0.1084 (11)	0.0582 (8)	0.0486 (8)	−0.0317 (8)	0.0048 (7)	0.0004 (6)
O1	0.0734 (8)	0.0500 (7)	0.0447 (7)	−0.0140 (6)	−0.0080 (6)	0.0094 (6)
N1	0.0647 (9)	0.0509 (8)	0.0395 (8)	−0.0130 (7)	0.0102 (7)	−0.0050 (6)
C9	0.0526 (10)	0.0451 (9)	0.0344 (8)	−0.0115 (7)	0.0079 (7)	0.0001 (7)
C3	0.0614 (11)	0.0620 (11)	0.0475 (10)	−0.0011 (9)	0.0056 (8)	0.0094 (9)
C4	0.0513 (10)	0.0520 (10)	0.0369 (8)	−0.0089 (8)	0.0077 (7)	0.0027 (7)
C10	0.0581 (10)	0.0434 (9)	0.0403 (9)	−0.0011 (8)	0.0115 (7)	0.0006 (7)
C8	0.0585 (10)	0.0470 (9)	0.0383 (9)	−0.0095 (8)	0.0023 (7)	0.0038 (7)
C6	0.0748 (13)	0.0603 (11)	0.0448 (10)	−0.0083 (10)	0.0175 (9)	−0.0107 (8)
C2	0.0687 (12)	0.0553 (11)	0.0659 (13)	0.0038 (9)	0.0160 (10)	0.0043 (9)
C12	0.0557 (10)	0.0539 (10)	0.0499 (10)	−0.0021 (8)	0.0051 (8)	0.0021 (8)
C11	0.0543 (10)	0.0435 (9)	0.0395 (9)	0.0061 (7)	0.0109 (7)	0.0039 (7)
C7	0.0650 (11)	0.0503 (10)	0.0543 (11)	−0.0005 (9)	0.0108 (9)	0.0003 (8)
C14	0.0805 (14)	0.0729 (14)	0.0418 (10)	0.0171 (11)	0.0008 (9)	0.0058 (9)
C5	0.0609 (11)	0.0663 (12)	0.0339 (9)	−0.0085 (9)	0.0080 (8)	−0.0027 (8)
C1	0.0717 (12)	0.0515 (10)	0.0564 (12)	−0.0082 (9)	0.0181 (9)	−0.0094 (9)
C13	0.0626 (12)	0.0755 (14)	0.0508 (11)	0.0014 (10)	−0.0047 (9)	−0.0035 (10)

Cl1—C5	1.7370 (18)	C4—C9	1.425 (2)
O1—C8	1.395 (2)	C5—C6	1.358 (3)
O1—C10	1.347 (2)	C6—C7	1.408 (3)
O2—C10	1.193 (2)	C6—H6	0.9300
O3—C11	1.364 (2)	C7—C8	1.355 (3)
O3—C14	1.361 (2)	C7—H7	0.9300
N1—C1	1.316 (2)	C8—C9	1.410 (2)
N1—C9	1.366 (2)	C10—C11	1.452 (2)
C1—C2	1.397 (3)	C11—C12	1.343 (2)
C1—H1	0.9300	C12—C13	1.413 (3)
C2—C3	1.356 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.330 (3)
C3—C4	1.410 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.414 (3)
C14—O3—C11	105.45 (15)	C1—C2—H2	120.3
C10—O1—C8	121.21 (13)	C11—C12—C13	106.20 (17)
C1—N1—C9	117.31 (15)	C11—C12—H12	126.9
N1—C9—C8	119.22 (14)	C13—C12—H12	126.9
N1—C9—C4	122.55 (16)	C12—C11—O3	110.63 (15)
C8—C9—C4	118.23 (15)	C12—C11—C10	132.30 (16)
C2—C3—C4	119.58 (17)	O3—C11—C10	117.05 (15)
C2—C3—H3	120.2	C8—C7—C6	119.90 (18)
C4—C3—H3	120.2	C8—C7—H7	120.0
C3—C4—C5	125.02 (16)	C6—C7—H7	120.0
C3—C4—C9	117.01 (16)	C13—C14—O3	111.11 (17)
C5—C4—C9	117.96 (16)	C13—C14—H14	124.4
O2—C10—O1	124.77 (16)	O3—C14—H14	124.4
O2—C10—C11	127.56 (16)	C6—C5—C4	122.09 (17)
O1—C10—C11	107.65 (14)	C6—C5—Cl1	119.07 (15)
C7—C8—O1	122.00 (17)	C4—C5—Cl1	118.83 (15)
C7—C8—C9	122.11 (16)	N1—C1—C2	124.20 (18)
O1—C8—C9	115.62 (15)	N1—C1—H1	117.9
C5—C6—C7	119.68 (17)	C2—C1—H1	117.9
C5—C6—H6	120.2	C14—C13—C12	106.60 (18)
C7—C6—H6	120.2	C14—C13—H13	126.7
C3—C2—C1	119.34 (19)	C12—C13—H13	126.7
C3—C2—H2	120.3
C1—N1—C9—C8	−179.10 (16)	C14—O3—C11—C10	178.79 (16)
C1—N1—C9—C4	0.3 (2)	O2—C10—C11—C12	179.9 (2)
C2—C3—C4—C5	−179.79 (18)	O1—C10—C11—C12	1.4 (3)
C2—C3—C4—C9	0.4 (3)	O2—C10—C11—O3	1.4 (3)
N1—C9—C4—C3	−0.7 (2)	O1—C10—C11—O3	−177.05 (15)
C8—C9—C4—C3	178.71 (15)	O1—C8—C7—C6	173.41 (16)
N1—C9—C4—C5	179.51 (16)	C9—C8—C7—C6	−0.4 (3)
C8—C9—C4—C5	−1.1 (2)	C5—C6—C7—C8	−1.2 (3)
C8—O1—C10—O2	2.3 (3)	C11—O3—C14—C13	−0.1 (2)
C8—O1—C10—C11	−179.13 (15)	C7—C6—C5—C4	1.6 (3)
C10—O1—C8—C7	59.4 (2)	C7—C6—C5—Cl1	−178.39 (14)
C10—O1—C8—C9	−126.42 (17)	C3—C4—C5—C6	179.78 (18)
N1—C9—C8—C7	−179.07 (17)	C9—C4—C5—C6	−0.4 (3)
C4—C9—C8—C7	1.5 (3)	C3—C4—C5—Cl1	−0.2 (3)
N1—C9—C8—O1	6.8 (2)	C9—C4—C5—Cl1	179.55 (12)
C4—C9—C8—O1	−172.65 (14)	C9—N1—C1—C2	0.4 (3)
C4—C3—C2—C1	0.2 (3)	C3—C2—C1—N1	−0.6 (3)
C13—C12—C11—O3	0.0 (2)	O3—C14—C13—C12	0.1 (2)
C13—C12—C11—C10	−178.50 (18)	C11—C12—C13—C14	−0.1 (2)
C14—O3—C11—C12	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.93	2.47	3.371 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.93	2.47	3.371 (2)	162

Symmetry code: (i) .